Limonen-1,2-oxide from orange

Researchers at Cornell have created a biodegradable polymer called polyfimonene carbonate, from limonene obtained from orange peel and converted to fimonene oxide, plus carbon dioxide. The polymer has properties similar to those of polystyrene and has potential to use carbon dioxide that would otherwise be emitted into the atmosphere, adding to the greenhouse effect. ... 

FIGURE 13.7 Oxidation of orange oil when plated on various base materials (Limonene oxide is an oxidation product of limonene, values mg/g limonene). (From Bolton, T.A., G.A. Reineccius, The oxidative stability and retention of a limonene-based model flavor plated on amorphous silica and other selected carriers, Perfum. Flavorist, 17, 2,1992. With permission.)... 

Brown (2000) evaluated VOC emissions from two of these products, as summarized in Table 16.6. Paint 1 was claimed to use orange peel oil as its base. It exhibited very high and fast-decaying emissions of C7-C10 alkane and limonene, with EF at 2 hours of 70000 and 120000 tgrn 2 h 1, respectively. Paint 2 was claimed to be based on vegetable oils and was virtually nonemitting at application, but emitted several malodorous aldehydes (including formaldehyde) and little else from 8 hours after application. This was considered to show an auto-oxidation reaction occurred for this product, similar to that observed with the alkyd enamel paint discussed earlier. 

A rapid loss of d-limonene, from 70 to 40 ppm for orange juice was observed in the 1 liter carton packs during the first days of ambient (25°C) storage (Fig. 4). Similar results were obtained by others (11,12) who claimed absorption by the film as the cause for this phenomenon. Again, the loss may vary between packages as shown in Fig. 5 The loss of d-limonene can be compensated for by increasing the initial d-limonene concentration. However, as d-limonene is a precursor to oxidative reactions of flavour compounds and since some flavour compounds are absorbed selectively at a higher rate, this is not desirable. 

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